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Scientific, Technical Publications in the Nuclear Field | IAEA �������� ����������������������������� ����� ������� ��������� ���� �������� ��� ��� ����� ������������ ��������� �������� ������ ��� ���� ���������������������������������������������� ������������������������������������������������� �������������� ������������� ��� ��������� �������� ������� ��������� �������� ��������� ������� ������� ���������� ���� �������� ������������ ������������� ���� ���� ���� ��������� ���� ���� ���������� ��� ��� ����������������������������������������������� � ����������������������������� ��� ��� ���� ������ ����� ��� ������������� ������������ ������������������������������������������������ ���������������������������������������������������������������� �������� ����������� ���� ����������� ����������� ��� �� ������ ������� ��� ������ ���������� ����� ��������� ������������ ������������������ ����������� �������������������� ���������������������������������� ������ ������������������ �������������� ������������������������������ ��������������������� LABELLING OF SMALL BIOMOLECULES USING NOVEL TECHNETIUM-99m CORES The following States are Members of the International Atomic Energy Agency: AFGHANISTAN GREECE NORWAY ALBANIA GUATEMALA PAKISTAN ALGERIA HAITI PALAU ANGOLA HOLY SEE PANAMA ARGENTINA HONDURAS PARAGUAY ARMENIA HUNGARY PERU AUSTRALIA ICELAND PHILIPPINES AUSTRIA INDIA POLAND AZERBAIJAN INDONESIA PORTUGAL BANGLADESH IRAN, ISLAMIC REPUBLIC OF QATAR BELARUS IRAQ REPUBLIC OF MOLDOVA BELGIUM IRELAND ROMANIA BELIZE ISRAEL RUSSIAN FEDERATION BENIN ITALY SAUDI ARABIA BOLIVIA JAMAICA SENEGAL BOSNIA AND HERZEGOVINA JAPAN SERBIA BOTSWANA JORDAN SEYCHELLES BRAZIL KAZAKHSTAN SIERRA LEONE BULGARIA KENYA SINGAPORE BURKINA FASO KOREA, REPUBLIC OF SLOVAKIA CAMEROON KUWAIT SLOVENIA CANADA KYRGYZSTAN SOUTH AFRICA CENTRAL AFRICAN LATVIA SPAIN REPUBLIC LEBANON SRI LANKA CHAD LIBERIA SUDAN CHILE LIBYAN ARAB JAMAHIRIYA SWEDEN CHINA LIECHTENSTEIN SWITZERLAND COLOMBIA LITHUANIA SYRIAN ARAB REPUBLIC COSTA RICA LUXEMBOURG TAJIKISTAN CÔTE D’IVOIRE MADAGASCAR THAILAND CROATIA MALAWI THE FORMER YUGOSLAV CUBA MALAYSIA REPUBLIC OF MACEDONIA CYPRUS MALI TUNISIA CZECH REPUBLIC MALTA TURKEY DEMOCRATIC REPUBLIC MARSHALL ISLANDS UGANDA OF THE CONGO MAURITANIA UKRAINE DENMARK MAURITIUS UNITED ARAB EMIRATES DOMINICAN REPUBLIC MEXICO UNITED KINGDOM OF ECUADOR MONACO GREAT BRITAIN AND EGYPT MONGOLIA NORTHERN IRELAND EL SALVADOR MONTENEGRO UNITED REPUBLIC ERITREA MOROCCO OF TANZANIA ESTONIA MOZAMBIQUE UNITED STATES OF AMERICA ETHIOPIA MYANMAR URUGUAY FINLAND NAMIBIA UZBEKISTAN FRANCE NETHERLANDS VENEZUELA GABON NEW ZEALAND VIETNAM GEORGIA NICARAGUA YEMEN GERMANY NIGER ZAMBIA GHANA NIGERIA ZIMBABWE The Agency’s Statute was approved on 23 October 1956 by the Conference on the Statute of the IAEA held at United Nations Headquarters, New York; it entered into force on 29 July 1957. The Headquarters of the Agency are situated in Vienna. Its principal objective is “to accelerate and enlarge the contribution of atomic energy to peace, health and prosperity throughout the world’’. TECHNICAL REPORTS SERIES No. 459 LABELLING OF SMALL BIOMOLECULES USING NOVEL TECHNETIUM-99m CORES INTERNATIONAL ATOMIC ENERGY AGENCY VIENNA, 2007 COPYRIGHT NOTICE All IAEA scientific and technical publications are protected by the terms of the Universal Copyright Convention as adopted in 1952 (Berne) and as revised in 1972 (Paris). The copyright has since been extended by the World Intellectual Property Organization (Geneva) to include electronic and virtual intellectual property. Permission to use whole or parts of texts contained in IAEA publications in printed or electronic form must be obtained and is usually subject to royalty agreements. Proposals for non-commercial reproductions and translations are welcomed and considered on a case-by-case basis. Enquiries should be addressed to the IAEA Publishing Section at: Sales and Promotion, Publishing Section International Atomic Energy Agency Wagramer Strasse 5 P. O. B o x 1 0 0 1400 Vienna, Austria fax: +43 1 2600 29302 tel.: +43 1 2600 22417 email: [email protected] http://www.iaea.org/books © IAEA, 2007 Printed by the IAEA in Austria November 2007 STI/DOC/010/459 IAEA Library Cataloguing in Publication Data Labelling of small biomolecules using novel technetium-99m cores. — Vienna : International Atomic Energy Agency, 2007. p. ; 24 cm. (Technical reports series, ISSN 0074–1914 ; no. 459) STI/DOC/010/459 ISBN 92–0–101607–7 Includes bibliographical references. 1. Biomolecules. 2. Technetium. 3. Radiolabeling. 4. Radio- pharmaceuticals. I. International Atomic Energy Agency. II. Series: Technical reports series (International Atomic Energy Agency) ; 459. IAEAL 07–00495 FOREWORD Technetium-99m radiopharmaceuticals, which were introduced in the mid-1960s, account for nearly 80% of all diagnostic studies performed in nuclear medicine. The ability to determine the exact molecular structure of coordination compounds by using modern powerful analytical tools such as nuclear magnetic resonance, mass spectroscopy and X ray diffraction helped in understanding the structure–activity relationships underlying the biological behaviour of 99mTc agents. Consequently, careful design of new ligands and their 99mTc complexes led to the discovery of imaging agents for perfusion in the myocardium and the brain. These developments significantly extended the scope of present day diagnostic imaging using 99mTc radiopharmaceuticals. The in vivo behaviour of new tracers is determined by their molecular properties, such as charge, lipophilicity and the reactivity of biologically active functional groups. Conversely, the current design of new generations of imaging agents is based on careful selection of suitable biomolecules that may function as effective vectors for in vivo delivery of activity to more specific biological targets such as receptors and transporters. This strategy implies that the labelling approach employed for introducing a radionuclide into the structure of a biomolecule should not lead to any distortion of that part of the molecule responsible for its biological activity. Thus the preparation of novel 99mTc imaging agents targeting selected biomolecular substrates would require the development of more sophisticated labelling approaches going beyond previous technologies. The IAEA organized a Consultants Meeting in 2002 at the University of Zurich, Switzerland, to assess the new developments in 99mTc labelling methodologies and the opportunities they might provide. The consultants + 2+ suggested that the low valent [Tc(CO)3] metal core and the [Tc(N)(PNP)] (PNP = heterodiphosphane) metal fragment offer new avenues for 99mTc radiolabelling of biologically active compounds. It was also identified that the 99mTc-(4 + 1) and 99mTc-HYNIC cores are versatile for developing new radiopharmaceuticals. The above four 99mTc cores offer the possibility to make 99mTc labelled small biomolecules with exceptionally high specific activity and with minimum alteration of the bioactivity of the ligand molecule. The coordinated research project (CRP) on Development of 99mTc Based Small Biomolecules Using Novel 99mTc Cores was started during 2003 with the specific objective to develop 99mTc labelled biomolecules with the above four novel 99mTc metal cores. Development of a few promising 99mTc labelled small biomolecules of high purity and stability for further investigation as potential radiopharmaceuticals was also expected as the outcome of this CRP. The first research coordination meeting (RCM) of the CRP was held in Ferrara, Italy, in May 2003, during which the participants made an overall workplan of the CRP based on the above objectives. The second RCM was held during November 2004 at IAEA Headquarters in Vienna, in which the participants reviewed the results obtained in the first part of the CRP and decided on the future directions. The final RCM was held in May 2006 in Budapest, in which the participants presented the results obtained by each participating laboratory and reviewed the overall achievements of the CRP. All the participants reported significant achievements in the application of the new labelling technologies based on the 99mTc-carbonyl, 99mTc-nitrido, 99mTc-(4 + 1) and 99mTc-HYNIC cores during the course of the CRP. The preparation, quality assessment and biological evaluation of a large number of 99mTc complexes with biomolecules such as RGD peptides, annexin derived peptides, fatty acid derivatives, quinazoline derivatives and glucose analogues were achieved. The biological evaluations of the different radiotracers were conducted in several laboratories, some with promising but most with negative biological uptakes. One notable development was the synthesis of 99mTc(N)(Cys2-Anx13) through a collaborative effort between Izotop, Hungary, and the Bhabha Atomic Research Centre, India. This 99mTc-nitrido complex showed specific binding to cultured apoptotic cells. Further investigations on this compound may enlighten the mechanism underlying this specific uptake and provide an opportunity for developing a novel radiopharmaceutical targeting apoptotic tissues. The participants were also successful in publishing a large number of scientific papers in peer reviewed journals. The results obtained by various laboratories during the course of the CRP are summarized in this report. The work reported is the culmination of the efforts of participants from Austria, Brazil, China, Germany, Greece, Hungary, Italy, India, Portugal, the Russian Federation, Switzerland, the United States of America and Uruguay. The
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